The gentleman’s guide to dressing timelessly

The guide to capturing the wardrobe essentials that ensure you'll never look out of season.

First, a confession: There’s no such thing as dressing “timelessly”. If you’ve paid any attention to, say, the way politicians dress vs. the way Tom Brady dresses, or the way Benedict Cumberbatch dresses (or maybe how Cary Grant once did), you’ll know that there’s no single way to dress, because fashion is constantly influencing the clothes that men wear.

Take the above example of politicians vs. people who look better than them, and you’ll quickly see why you can’t just dress the same way forever: eventually you look like an out-of-touch fossil—and perhaps out of touch, not just with fashion, but with society in general. If that’s a bad look for a politico, think how terrible it’ll make anyone else look, too.

Still: There’s an art to building a wardrobe with elements you won’t have to replace every season. To learn that art, we asked Bonobos’ Chief Creative Officer Dwight Fenton, a 20-year style veteran who’s also worked at Patagonia and J. Crew.

Fenton’s main concept: The modern way to consistently dress well is to mix casual pieces with more formal ones. In fact, being just slightly “off-trend” is what timeless dressing is all about. Your sense of style should be about self-expression, not total conformity. Observe the trend without being a slave to the moment. That’s something any guy can do with straightforward, foundational clothing.

Here are 10 tips you can use to dress well—and maybe even a little bit “timelessly”.

1. Invest in quality shoes

Footwear trends for men don’t change radically, Fenton says. “They may get a little pointier, but the shapes only change subtly.” Higher-end shoemakers like Alden or Church’s utilize “Goodyear welt” construction, which enables the shoes to be resoled, Fenton says. Resoling can help shoes last longer than a decade—so while up-front footwear cost might seem high, shoes are still smart style investments. Higher-end shoes are more likely to be available in wide widths. “Right out of the box, they’ll actually fit your feet. And they’re using far better construction methods” that have literally evolved over centuries, Fenton says.

Courtesy of Edward Green

2. Give yourself some footwear range

Guys can also get away with having a few do-it-all pairs of shoes. A pair of penny loafers never goes out of style, Fenton says. Cordovan oxfords or wingtips are slightly more stylish, and afford you a lot of range in your outfits. Monkstraps are having a fashionable comeback, and “they’re sort of always in style, if you want to effect a more British sensibility,” Fenton notes.

And while sneakers-with-suits is a popular trend at the moment, you can easily get away with chukka-style boots instead. Even some “dressier” hiking boots can work with a sport coat and dark indigo jeans, but you probably shouldn’t wear anything too utilitarian if you’re wearing a three-piece suit and a bowtie.

Richard Bol / Getty

3. Buy the right suit

These days, suits are cut to look athletic, slim, slightly shorter, and more tapered. “When I graduated from college my dad thought he was doing me a favor giving me his old suits, and they had these ridiculous-looking wide lapels and huge, padded shoulders,” Fenton says. That’s not a dig at his dad—point is, even if a blue suit seems timeless, its shape is not.

Also critical: Don’t cheap out on your suits. “When they’re two-for-$400 or whatever, the manufacturer has had to cut corners”—sometimes literally, he says. One test: Pull at the lapels or the pocket flaps. These portions can literally be glued together, and on cheaper suits, the felt lapel backing might not fit quite right. “Suits are the most complicated items you can make in the world of menswear,” he says. “Just setting the sleeve so it hangs right is true artisan stuff.”

Another test: Try on a suit that’s at the high end of your budget, and then try a more economical model. Take selfies at both shops and see how you look. Stride around the store. A good suit is actually constructed to move with you, not resist movement, and you can actually feel the difference.

From there, get the staples. Fenton suggests a blue suit. And while brighter blue hues are popular at the moment, you can't go wrong with grey flannel, or lighter-weight, three-season suits in traditional charcoal hues. Chunkier herringbone patterns and plaids are very much in style, and while the former is classic, he suggests staying relatively conservative if the goal is to build timeless pieces for your closet. One timeless tip: A little plaid always goes a very long way.

Caiaimage/Lukas Olek / Getty

4. Get your suit (and anything else that doesn’t quite fit) Tailored.

Fit is everything—not just when it comes to suits, but for every item you wear. If you’re in shape, you want your clothing to show that, not hide it. Athletic fits aren’t just “in”—timeless dressing has always looked better on fit men. Even in the blousy '70s, if you were dressing from Saville Row (and were in good shape), your clothing would show off your body.

Athletic suit designs these days mean that Bonobos (and labels like J. Crew and Todd Snyder) are building suits “to accommodate a more built guy, whose shoulders are a little bigger, and whose chest is bigger,” says Fenton. Brands focused on fit guys tend to use traditional tailoring, but dramatically narrow the taper from shoulder to waist.

Courtesy of Bonobos

5. Unite the right trousers with your jackets

Our current denim-with-sportcoat moment seems like it’s here to say, Fenton says—and a good pair of jeans is always a smart investment. That said, the classic wardrobe should include some quality dark denim, a casual pair of chinos, a pair of dress chinos.

Most important: “Pay attention to fit and texture,” Fenton says. When you’re matching the pants with the jacket, or the corduroy trouser with the sport coat, the feel of the top and bottom pieces should complement each other—not matching, but not feuding either. While cuffs on trousers (especially suit trousers) are back in style for some guys, pants are still being hemmed with no break (meaning they shouldn’t touch your shoe tops).

In any case, when you’re choosing pants to go with the jacket or a blazer, the game is all about having enough variety to play off the jacket’s more traditional “framing”. If the jacket is more conservative, add more color and texture to the trouser.

Courtesy of Bonobos

6. Know when to wear a tie (and what kind to wear)

There’s still a place for wearing a tie, but it’s all about setting. Increasingly, getting “dressed up” means wearing a suit without a tie—and that’s allowed Bonobos and other brands to have more fun with shirting.

“Bonobos has shirts with tigers or birds in patterns on them,” Fenton points out. Does Bonobos think men will wear those shirts with ties? Not necessarily, Fenton says. A heavily patterned shirt creates visual "noise" in an outfit, so you don't necessarily need to wear a tie with it. You can complement that patterned shirt with "quieter" trousers, sport coat, or other layers that will take a visual back seat.

Murat Ozdemir/Corbis/VCG / Getty

7. Get to know your shirt collars

As with suits, the fit of shirts these days is more athletic, but tapers as well—so you’re not left with a lot of blousing. The collar should fit your face. There are multiple collar shapes and widths to match the dimensions of your mug, and, in general, narrow works better with slimmer, more angular faces, and adding width to the collar mates better with wider, rounder features. Consider button-downs, too, especially with a casual, chunky tie, or for wearing under a V-neck sweater and a tweed jacket.

Morsa Images / Getty

8. Pick up the essential shirts for every occasion

Get a traditional blue oxford shirt or two, and several “broadcloth” whites. Yes, you should explore more than that, but these hues (or hue-less) shirts work with everything else, which is why they’re standard fare for every man’s closet.

Beyond that, pinstripes always work, and ginghams of all sorts are both very much in fashion these days, and relatively timeless, too. And a relatively noisy pattern like gingham, by the way, lets you play in the shirt-as-tie realm, without having a shirt full of parakeets.

Courtesy of Bonobos

9. Tie one on

Choosing ties, Fenton says, is the same game it’s always been. Ties have grown slightly wider at retail than in the past few years, with 2.75-to-3" about the norm, but 2.5" is still a perfectly acceptable width.

As with footwear and suits, don’t get too cheap with your ties. Beautiful ties not only feel better because they incorporate better silks, but are also constructed more carefully. “They last longer, too, so you can get the knot right for years without them losing their shape,” Fenton says.

Better-made neckwear is cooler, too, because the lining is designed to breathe. As for worrying about trends changing and ties widening or narrowing? The giant widths of the ’70s may never come back, but there’s room for going slimmer or slightly wider than the trend without looking clueless, Fenton says.

FluxFactory / Getty

10. Accessorize, but do not bling

Accessories are one of those areas where guys should defer to their comfort zones. From chain wallets to nose piercings to fistfuls of rings, accessories are deeply personal and generally best used when you’re already comfortable wearing them. But in the context of dressing timelessly, jewelry for guys is a lot like plaid: Use it sparingly.

And by the way, jewelry fits within the larger context of accessories: loud socks with a quiet suit; your Uncle Louie’s goofy gold tie bar from the Elks Lodge; wild-patterned ties; pocket squares.

Whenever accessorizing, follow this rule of thumb from Fenton: add a hint of complexity, but not too much. When in doubt, essentials will always be timeless.